2-Naphthalenesulfonyl chloride → N-(2-{[(3-Hydroxypropyl)amino]methyl}-3,4-dihydro-2H-chromen-7-yl)naphthalene-2-sulfonamide

HRID 49462

Reaction equation

[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:12]O)[O:9]2)=[CH:4][CH:3]=1.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[S:24](Cl)(=[O:26])=[O:25].[NH2:28][CH2:29][CH2:30][CH2:31][OH:32]>N1C=CC=CC=1.O>[OH:32][CH2:31][CH2:30][CH2:29][NH:28][CH2:12][CH:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:2]([NH:1][S:24]([C:15]3[CH:16]=[CH:17][C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:14]=3)(=[O:26])=[O:25])=[CH:3][CH:4]=2)[O:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of (7-amino-3,4-dihydro-2H-chromen-2-yl)methanol (25 mg, 140 μmol) in pyridine is treated with 2-naphthalenesulfonylchloride (70 mg, 308 μmol) at ambient temperature for 1 h, treated with 3-amino-1-propanol (3 mmol, 0.23 mL), heated at 80° C. for 3 h, diluted with water and extracted with ethyl acetate. The extracts are combined, dried over Na2SO4 and concentrated in vacuo. The resultant residue is purified by reverse phase preparative HPLC to give the title product, M+H 427, retention time 7.92 min.

Workup

extractionextracted with ethyl acetate
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe resultant residue is purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-b252316eb42d4f76a074015cae6cf308
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706757B2

Linked notes

Loading…